Heat oven to 350 degrees F. Toast almonds on large baking sheet in 350 degree F oven for 10 minutes or until fragrant and lightly golden. Let cool slightly. Line second large sheet with waxed paper.
Stuff each date with an almond, snipping one end of the date if the opening is too small. Finely chop or grind remaining almonds.
Melt semisweet chocolate and 1 teaspoon oil in microwave-safe bowl in microwave on high for 1 minute, stirring until smooth. Dip half the dates into semisweet chocolate, coating evenly. Use a fork to remove, allowing excess to drip into bowl. Place on waxed paper-lined sheet.
Melt milk chocolate and remaining oil as above. Dip remaining dates. Chill all dates 30 minutes or until firm.
Remove dates from refrigerator. Remelt chocolates, if necessary. Dip end in different chocolate, then in ground almonds. Set on waxed paper. Chill until firm.